UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
Enzymatic synthesis of N-hydroxyalkyl fatty acid amides of analogs of anandamide
Autor/es:
GUADALUPE GARCÍA LIÑARES; PAULA G. QUINTANA; SANTIAGO N. CHANQUÍA; ALICIA BALDESSARI
Lugar:
Estambul
Reunión:
Congreso; 15th European Congress on Biotechnology 2012; 2012
Resumen:
Enzymatic synthesis of N-hydroxyalkyl-fatty acid amides analogs of anandamide Guadalupe García Liñares, Paula G. Quintana, Santiago N. Chanquía and Alicia Baldessari Laboratorio de Biocatálisis. Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina. alib@qo.fcen.uba.ar Endogenous cannabinoids, called endocannabinoids, function as agonists of the cannabinoid receptors CB1 and CB2. They are fatty acid amides (FAA), being arachidonyl-2?-ethanolamide known as anandamide, the most relevant member of this family of compounds. Endocannabinoids show a potent biological activity on central nervous system and various methabolic systems. They are interesting therapeutic agents used in treatment of pain, anxiety and sleep disorders, show antiinflamatory and analgesic effects, etc. Regarding others metabolic effects, FAA can regulate the food intake, obesity and diabetes. In physiological conditions, anandamide is rapidly hydrolyzed by fatty acid amide hydrolase, the enzyme responsible for its degradation to arachidonic acid and ethanolamine. With the aim to lengthen the activity of anandamide, in this work we report the synthesis of a series of FAA by reaction of omega-3 and omega-6 fatty acid ethyl esters with various alkanolamines through an enzymatic approach. Candida antarctica lipase was selected as biocatalyst and reaction parameters were studied (temperature, E/S, alcohol and alkanolamine/fatty acid, time, solvent, free-solvent system, etc.) to achieve the optimal reaction conditions. We also describe a procedure for the one-pot, two-steps conversion of the fatty acids into anandamide analogs via in situ formation of the ethyl ester and subsequent aminolysis by the alkanolamine. The products, most of them novel compounds, were obtained in high yield (70-98%) and the enzyme showed a chemoselective behavior in relation to hydroxyl- and amino groups affording the fatty acids alkanolamides as the only reaction products.